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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-09-11 00:41:42 UTC
Update Date2020-02-26 21:26:55 UTC
HMDB IDHMDB0006941
Secondary Accession Numbers
  • HMDB06941
Metabolite Identification
Common NameL-2-Aminoadipate adenylate
DescriptionL-2-Aminoadipate adenylate is an intermediate in Lysine biosynthesis. L-2-Aminoadipate adenylate is the 4th to last step in the synthesis of L-Lysine and is converted from L-2-Aminoadipate via the enzyme aminoadipate-semialdehyde dehydrogenase (EC 1.2.1.31). It is then converted to alpha-Aminoadipoyl-S-acyl enzyme via the enzyme aminoadipate-semialdehyde dehydrogenase (EC 1.2.1.31).
Structure
Data?1582752415
Synonyms
ValueSource
L-2-Aminoadipic acid adenylic acidGenerator
5-Adenylyl-2-aminoadipateHMDB
alpha-Aminoadipoyl-C6-AMPHMDB
(2S)-2-Amino-6-[({[(3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-6-oxohexanoateGenerator
Chemical FormulaC16H23N6O10P
Average Molecular Weight490.3618
Monoisotopic Molecular Weight490.121327498
IUPAC Name(2S)-2-amino-6-[({[(3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-6-oxohexanoic acid
Traditional Name(2S)-2-amino-6-({[(3S,4R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-6-oxohexanoic acid
CAS Registry NumberNot Available
SMILES
N[C@@H](CCCC(=O)OP(O)(=O)OCC1OC([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O
InChI Identifier
InChI=1S/C16H23N6O10P/c17-7(16(26)27)2-1-3-9(23)32-33(28,29)30-4-8-11(24)12(25)15(31-8)22-6-21-10-13(18)19-5-20-14(10)22/h5-8,11-12,15,24-25H,1-4,17H2,(H,26,27)(H,28,29)(H2,18,19,20)/t7-,8?,11+,12+,15?/m0/s1
InChI KeyPOJWEBKSMOTPNS-ILUWSIKFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent5'-acylphosphoadenosines
Alternative Parents
Substituents
  • 5'-acylphosphoadenosine
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Acyl phosphate
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Fatty acyl
  • Phosphoric acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Pyrimidine
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • 1,2-diol
  • Carboxylic acid salt
  • Amino acid
  • Amino acid or derivatives
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic salt
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.31 g/LALOGPS
logP-2.2ALOGPS
logP-6.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.78ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area255.46 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity106.46 m³·mol⁻¹ChemAxon
Polarizability43.51 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-5964200000-acdda8931d3ab87181dbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-5770945000-7020e281db779956ae78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1911500000-804e1e358cbe4d6ed7e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-5749eb7dc870f8022bc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4900000000-667c1cf3b76819c1d461Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03ni-8775900000-afc9a641c5c823212705Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-7911000000-4324a475bbd0937df5faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9500000000-c83f1bc791359b441bc2Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024157
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05560
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477910
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
Aminoadipic acid + Adenosine triphosphate → L-2-Aminoadipate adenylate + Pyrophosphatedetails
L-2-Aminoadipate adenylate + Holo-Lys2 → alpha-Aminoadipoyl-S-acyl enzyme + Adenosine monophosphatedetails
General function:
Involved in acyl carrier activity
Specific function:
Acyl-CoA synthases catalyze the initial reaction in fatty acid metabolism, by forming a thioester with CoA
Gene Name:
AASDH
Uniprot ID:
Q4L235
Molecular weight:
122596.1
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the post-translational modification of target proteins by phosphopantetheine. Can transfer the 4'-phosphopantetheine moiety from coenzyme A to a serine residue of a broad range of acceptors, such as the acyl carrier domain of FASN.
Gene Name:
AASDHPPT
Uniprot ID:
Q9NRN7
Molecular weight:
35775.64